EP1492833A1 - Water curable polyurethane compositions and uses thereof - Google Patents
Water curable polyurethane compositions and uses thereofInfo
- Publication number
- EP1492833A1 EP1492833A1 EP03746575A EP03746575A EP1492833A1 EP 1492833 A1 EP1492833 A1 EP 1492833A1 EP 03746575 A EP03746575 A EP 03746575A EP 03746575 A EP03746575 A EP 03746575A EP 1492833 A1 EP1492833 A1 EP 1492833A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- mdi
- nco
- water
- polyisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 238
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 103
- 239000004814 polyurethane Substances 0.000 title description 8
- 229920002635 polyurethane Polymers 0.000 title description 8
- 229920005989 resin Polymers 0.000 claims abstract description 70
- 239000011347 resin Substances 0.000 claims abstract description 70
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 65
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 65
- 238000009472 formulation Methods 0.000 claims abstract description 28
- 230000009257 reactivity Effects 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000005187 foaming Methods 0.000 claims description 46
- 239000004014 plasticizer Substances 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229920005862 polyol Polymers 0.000 claims description 37
- 150000003077 polyols Chemical class 0.000 claims description 36
- 239000004615 ingredient Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 239000002516 radical scavenger Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 11
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 10
- 230000003254 anti-foaming effect Effects 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 239000010690 paraffinic oil Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 abstract description 35
- 150000002513 isocyanates Chemical class 0.000 abstract description 34
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 abstract description 21
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 16
- 239000002904 solvent Substances 0.000 abstract description 14
- 230000008901 benefit Effects 0.000 abstract description 11
- 239000000470 constituent Substances 0.000 abstract description 9
- 239000007787 solid Substances 0.000 abstract description 7
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 150000003673 urethanes Chemical class 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 2
- 230000036541 health Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 38
- 239000003054 catalyst Substances 0.000 description 30
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 29
- 229910002092 carbon dioxide Inorganic materials 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 230000006870 function Effects 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 239000004970 Chain extender Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- -1 isocyanate compound Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000012855 volatile organic compound Substances 0.000 description 5
- 229920002176 Pluracol® Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 238000009408 flooring Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000009428 plumbing Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BCSGAWBQJHXXSE-UHFFFAOYSA-N bis(11-methyldodecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC(C)C BCSGAWBQJHXXSE-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- RKELNIPLHQEBJO-UHFFFAOYSA-N bis(5-methylhexyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC(C)C RKELNIPLHQEBJO-UHFFFAOYSA-N 0.000 description 1
- LGBAGUMSAPUZPU-UHFFFAOYSA-N bis(9-methyldecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC(C)C LGBAGUMSAPUZPU-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 238000009156 water cure Methods 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
- C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/708—Isocyanates or isothiocyanates containing non-reactive high-molecular-weight compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
Definitions
- compositions may be used as glue and/or applied, coated, trowelled, poured, shaped, sprayed, injected, rolled, brushed, or otherwise used to form structures of any desired thickness, including coatings, membranes, skid-resistant surfaces, plugs, gaskets, caulking, crack fillers, seals, encapsulation, three dimensional structures, and the like.
- Embodiments of water curable polyurethane compositions are commercially available. These have advantageously been used as base and/or top coatings over commercial and residential floors or other walkways, roofing, plumbing, piping, columns or other architectural items, zoo enclosures, decking in marine environments, exterior walkways, and the like.
- the ability to use a slower reacting MDI isomer in combination with a faster reacting isocyanate material such as 4,4'- MDI allows the curing characteristics (e.g., pot life and the like) to be fairly precisely tailored for specific applications merely be adjusting the relative amounts of the faster and slower reacting isocyanates in the formulation.
- Another key advantage of using one or more sterically hindered MDI isomers in a formulation relates to the urethane/urea content of the resultant compositions when cured.
- any such oligomers and/or polymers may be thermoplastic materials that form a semi-interpenetrating polymer network with the NCO functional resin upon curing. Additionally, such materials may be miscible with the NCO-functional resin so that blends are a single phase. Alternatively, such materials may be wholly or partially immiscible with the NCO functional resin in some instances so that the materials physically crosslink. When such other material(s) are used, the weight ratio of the NCO-functional resin to such other material(s) may be in the range of from about 1 :20 to 20: 1.
- the branched, polar plasticizers such as the branched phthalates have foam-alleviating characteristics.
- incorporating at least one of these materials into the compositions of the invention is highly preferred to help facilitate the use of higher NCO content and/or more reactive NCO moieties.
- These plasticizers are particularly useful in helping to reduce foaming activity when the polyisocyanate component of the preferred NCO functional resin includes an isomer, or mixture of isomers, of MDI.
- diisononyl phthalate DINP
- DINP diisononyl phthalate
- Moisture scavenger p-toluene sulfonyl isocyanate Sufficient amount to obtain moisture content of no more than 0.02%
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37125302P | 2002-04-09 | 2002-04-09 | |
| US371253P | 2002-04-09 | ||
| PCT/US2003/010001 WO2003087185A1 (en) | 2002-04-09 | 2003-04-01 | Water curable polyurethane compositions and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1492833A1 true EP1492833A1 (en) | 2005-01-05 |
Family
ID=29250661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03746575A Withdrawn EP1492833A1 (en) | 2002-04-09 | 2003-04-01 | Water curable polyurethane compositions and uses thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6870000B2 (enExample) |
| EP (1) | EP1492833A1 (enExample) |
| JP (1) | JP2005522544A (enExample) |
| KR (1) | KR20040098059A (enExample) |
| CN (1) | CN1310993C (enExample) |
| AU (1) | AU2003226191A1 (enExample) |
| WO (1) | WO2003087185A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6870000B2 (en) * | 2002-04-09 | 2005-03-22 | Laxmi C. Gupta | Water curable polyurethane compositions and uses thereof |
| US7148287B2 (en) * | 2003-05-15 | 2006-12-12 | Gupta Laxmi C | Water curable polyurethane compositions with improved viscosity characteristics |
| US20050277724A1 (en) * | 2004-05-26 | 2005-12-15 | Jon Pavlinac | Sprayable elastomer composition |
| US7256249B2 (en) * | 2004-06-02 | 2007-08-14 | Acushnet Company | Compositions for golf equipment |
| US20070083003A1 (en) * | 2005-10-11 | 2007-04-12 | Gupta Laxmi C | Water curable polyurethane compositions and uses thereof |
| DE102007001868A1 (de) * | 2007-01-12 | 2008-07-17 | Bayer Materialscience Ag | Polyurethan-Dispersionen auf Basis von 2,2'MDI |
| US8178204B2 (en) * | 2008-03-05 | 2012-05-15 | Bayer Materialscience Llc | Acrylate-modified aspartates and gel coat compositions made therefrom |
| US20090226644A1 (en) * | 2008-03-05 | 2009-09-10 | Wylie Amy S | Gel coat compositions from acrylate-modified aspartates |
| CA2738910C (en) * | 2008-09-30 | 2016-02-02 | Henkel Corporation | Dry-to-the-touch moisture-curable compositions and products made therefrom |
| CN102181225A (zh) * | 2011-01-31 | 2011-09-14 | 北京东方雨虹防水技术股份有限公司 | 水固化聚氨酯防水涂料 |
| KR101195107B1 (ko) | 2012-04-05 | 2012-10-29 | 광진산업(주) | 폴리우레탄 바닥재 제조방법 및 그에 의해 제조된 바닥재 |
| RU2685276C2 (ru) * | 2014-06-19 | 2019-04-17 | Хантсмэн Интернэшнл Ллс | Силилированные полиуретаны |
| CN107760245A (zh) * | 2016-08-18 | 2018-03-06 | 摩田化学（昆山）有限公司 | 面料复合用pur反应型热熔胶及其制备方法 |
| CN112679157A (zh) * | 2020-12-17 | 2021-04-20 | 江苏长路交通工程有限公司 | 一种半刚性基层裂缝非开挖注浆修补材料及其制备方法 |
| KR102424810B1 (ko) | 2021-10-25 | 2022-07-25 | 좌운선 | 친환경 폴리우레탄 합성수지를 포함하는 접착성과 내마모성 및 미끄럼저항성이 우수한 콘크리트 포장재 및 이를 이용한 시공방법 |
| KR102374512B1 (ko) | 2021-10-25 | 2022-03-15 | 좌운선 | 친환경 폴리우레탄 합성수지를 포함하는 난연성과 미끄럼저항성 및 소음차단기능이 우수한 콘크리트 바닥재 및 이를 이용한 시공방법 |
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| US7148287B2 (en) * | 2003-05-15 | 2006-12-12 | Gupta Laxmi C | Water curable polyurethane compositions with improved viscosity characteristics |
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2003
- 2003-03-31 US US10/403,647 patent/US6870000B2/en not_active Expired - Lifetime
- 2003-04-01 WO PCT/US2003/010001 patent/WO2003087185A1/en not_active Ceased
- 2003-04-01 EP EP03746575A patent/EP1492833A1/en not_active Withdrawn
- 2003-04-01 CN CNB038097974A patent/CN1310993C/zh not_active Expired - Fee Related
- 2003-04-01 JP JP2003584139A patent/JP2005522544A/ja active Pending
- 2003-04-01 KR KR10-2004-7015944A patent/KR20040098059A/ko not_active Ceased
- 2003-04-01 AU AU2003226191A patent/AU2003226191A1/en not_active Abandoned
-
2005
- 2005-02-28 US US11/069,530 patent/US20050148678A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
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| See references of WO03087185A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003087185A1 (en) | 2003-10-23 |
| CN1649928A (zh) | 2005-08-03 |
| US20050148678A1 (en) | 2005-07-07 |
| JP2005522544A (ja) | 2005-07-28 |
| US20030191235A1 (en) | 2003-10-09 |
| AU2003226191A1 (en) | 2003-10-27 |
| KR20040098059A (ko) | 2004-11-18 |
| US6870000B2 (en) | 2005-03-22 |
| CN1310993C (zh) | 2007-04-18 |
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